ethyl 1-ethyl-7-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate | 51624-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 1-ethyl-7-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: 1-ethyl-7-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester；ethyl 1-ethyl-1,4-dihydro-7-nitro-4-oxo-3-quinolinecarboxylate；ethyl 1-ethyl-7-nitro-4-oxoquinoline-3-carboxylate
• CAS: 51624-72-7
• 化学式: C₁₄H₁₄N₂O₅
• 分子量: 290.276
• InChiKey: WOBUEWWPMHKVMW-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C(Solv: ethanol (64-17-5))
• 沸点：
  444.0±45.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-ethyl-7-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 1-ethyl-3-carbethoxy-7-amino-4-oxo-1,4-dihydroquinoline
  参考文献：
  名称：

  新型乙基（取代的）苯基-4-氧噻唑烷-1--3-基）-1-乙基-4-氧-1,4-二氢喹啉-3-羧酸盐作为潜在的抗癌剂

  摘要：

  一系列乙基（取代的）苯基-4-氧噻唑啉-3-基）-1-乙基-4-氧代-1,4-二氢喹啉-3-羧酸盐（7a，7b，7c，7d，7e，7f，7g）由氨基喹诺酮类6与戊醛和巯基乙酸之间的反应制备。临界中间体，6 a和6b中，从适当的胺通过涉及与diethylethoxymethylenemalonate（ⅰ）反应，（ⅱ）在二苯醚热环化，（ⅲ）乙基和（iv）的Pd / C催化的还原步骤的序列而获得。新化合物7a，7b，7c，7d，7e，7f，7g可以通过NMR（1 H和13 C）完全鉴定和表征，尤其是X射线晶体学可以鉴定7d。发现化合物7b，7c，7d，7e，7f在10uM浓度下不表现出抗胃炎（AGP‐01），胃腺癌样小肠（ACP‐02），结肠（HCT‐116）和鼠类黑色素瘤（B16F10）的活性）癌细胞。但是，没有一种对正常细胞人成纤维细胞（MRC-5），鼠成纤维细胞（NIH3T3）和正常人黑素细胞（Melan-A）表现出细胞毒性。

  DOI：

  10.1002/jhet.2212
• 作为产物：
  描述：

  二乙基(3-硝基苯胺亚甲基)丙二酸 以 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 ethyl 1-ethyl-7-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  1,2,3-Triazolyl-4-oxoquinolines: A feasible beginning for promising chemical structures to inhibit oseltamivir-resistant influenza A and B viruses

  摘要：

  We described the synthesis of a new congener series of 1,2,3-triazolyl-4-oxoquinolines and evaluated their ability to inhibit oseltamivir (OST)-resistant influenza strains. Oxoquinoline derivative 1i was the most potent compound within this series, inhibiting 94% of wild-type (WT) influenza neuraminidase (NA) activity. Compound 1i inhibited influenza virus replication with an EC50 of 0.2 mu M with less cytotoxicity than OST, and also inhibited different OST-resistant NAs. These results suggest that 1,2,3-triazolyl-4-oxoquinolines represent promising lead molecules for further anti-influenza drug design. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2015.11.028

文献信息

• 1-Alkyl-1,4-dihydro-4-oxo-7-triazenyl-3-quinolinecarboxylic acids
  申请人：Sterling Drug Inc.

  公开号：US04137227A1

  公开（公告）日：1979-01-30

  Compounds useful as antibacterial agents are 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylic acids (I), wherein: (a) BN is dimethylamino where R is methyl, ethyl, n-propyl, n-butyl, n-pentyl or n-octyl; (b) BN is diethylamino where R is n-propyl; or, (c) BN is 4-methyl-1-piperazinyl where R is ethyl. These compounds are prepared by reacting lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) with a mineral acid and an alkali nitrite in aqueous medium to produce the corresponding diazonium salt of said 7-aminoquinoline, reacting said diazonium salt with an amine of the formula BNH in the presence of an acid-acceptor to produce lower-alkyl 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylate and hydrolyzing said 3-quinolinecarboxylate to produce the corresponding 3-carboxylic acid (I). The intermediate lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) are prepared in several steps by conventional means starting with m-aniline.

  有用作抗菌剂的化合物为1-R-1,4-二氢-4-氧代-7-(BN--N.dbd.N)-3-喹啉羧酸(I)，其中：(a)当R为甲基、乙基、正丙基、正丁基、正戊基或正辛基时，BN为二甲基氨基；(b)当R为正丙基时，BN为二乙基氨基；(c)当R为乙基时，BN为4-甲基-1-哌嗪基。这些化合物通过将较低烷基7-氨基-1-R-1,4-二氢-4-氧代-3-喹啉羧酸酯(II)与矿酸和碱性硝酸盐在水介质中反应，制备出相应的7-氨基喹啉的重氮盐，将该重氮盐与式为BNH的胺在酸受体的存在下反应，制备出较低烷基1-R-1,4-二氢-4-氧代-7-(BN--N.dbd.N)-3-喹啉羧酸酯，并水解该3-喹啉羧酸酯以制备相应的3-羧酸(I)。中间体较低烷基7-氨基-1-R-1,4-二氢-4-氧代-3-喹啉羧酸酯(II)通过常规方法从间苯二胺开始进行数步制备。
• An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors
  作者：Davide Benedetto Tiz、Žiga Skok、Martina Durcik、Tihomir Tomašič、Lucija Peterlin Mašič、Janez Ilaš、Anamarija Zega、Gábor Draskovits、Tamás Révész、Ákos Nyerges、Csaba Pál、Cristina D. Cruz、Päivi Tammela、Dušan Žigon、Danijel Kikelj、Nace Zidar

  DOI：10.1016/j.ejmech.2019.02.004

  日期：2019.4

  ATP competitive inhibitors of DNA gyrase and topoisomerase IV have great therapeutic potential, but none of the described synthetic compounds has so far reached the market. To optimise the activities and physicochemical properties of our previously reported N-phenylpyrrolamide inhibitors, we have synthesized an improved, chemically variegated selection of compounds and evaluated them against DNA gyrase and topoisomerase IV enzymes, and against selected Gram-positive and Gram-negative bacteria. The most potent compound displayed IC50 values of 6.9 nM against Escherichia coli DNA gyrase and 960 nM against Staphylococcus aureus topoisomerase IV. Several compounds displayed minimum inhibitory concentrations (MICs) against Gram-positive strains in the 1-50 mu M range, one of which inhibited the growth of Enterococcus faecalis, Enterococcus faecium, S. aureus and Streptococcus pyogenes with MIC values of 1.56 mu M, 1.56 mu M, 0.78 mu M and 0.72 mu M, respectively. This compound has been investigated further on methicillin-resistant S. aureus (MRSA) and on ciprofloxacin non-susceptible and extremely drug resistant strain of S. aureus (MRSA VISA). It exhibited the MIC value of 2.5 mu M on both strains, and MIC value of 32 mu M against MRSA in the presence of inactivated human blood serum. Further studies are needed to confirm its mode of action. (C) 2019 Elsevier Masson SAS. All rights reserved.
• AGUI H.; KOMATSU T.; NAKAGOME T., J. HETEROCYCL. CHEM. <JHTC-AD>, 1975, 12, NO 3, 557-563,
  作者：AGUI H.、 KOMATSU T.、 NAKAGOME T.

  DOI：——

  日期：——
• US4137227A
  申请人：——

  公开号：US4137227A

  公开（公告）日：1979-01-30
• 1,2,3-Triazolyl-4-oxoquinolines: A feasible beginning for promising chemical structures to inhibit oseltamivir-resistant influenza A and B viruses
  作者：Fernanda da C.S. Boechat、Carolina Q. Sacramento、Anna C. Cunha、Fernanda S. Sagrillo、Christiane M. Nogueira、Natalia Fintelman-Rodrigues、Osvaldo Santos-Filho、Cecília S. Riscado、Luana da S.M. Forezi、Letícia V. Faro、Leonardo Brozeguini、Isakelly P. Marques、Vitor F. Ferreira、Thiago Moreno L. Souza、Maria Cecília B.V. de Souza

  DOI：10.1016/j.bmc.2015.11.028

  日期：2015.12

  We described the synthesis of a new congener series of 1,2,3-triazolyl-4-oxoquinolines and evaluated their ability to inhibit oseltamivir (OST)-resistant influenza strains. Oxoquinoline derivative 1i was the most potent compound within this series, inhibiting 94% of wild-type (WT) influenza neuraminidase (NA) activity. Compound 1i inhibited influenza virus replication with an EC50 of 0.2 mu M with less cytotoxicity than OST, and also inhibited different OST-resistant NAs. These results suggest that 1,2,3-triazolyl-4-oxoquinolines represent promising lead molecules for further anti-influenza drug design. Published by Elsevier Ltd.